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4. American Music Awards

Image via Getty/Kevin Mazur/WireImage

WHEN: 2008

When you think of the now-defunct Pastelle, this outfit should be the first image that comes to mind. The flashy jacket with the even flashier patchwork on the back has been on every Kanye fan's wishlist since its first appearance. Which is why the news that Kanye deaded Pastelle was even harder to take.